First Impressions
by skimmy77
Summary: A "what if" fic. What if Oliver and Felicity had met during their college years? Rated T just in case.
1. Chapter 1

**A/N: Based on the recent spoilers for 3x05, where we meet Goth!Felicity, and I thought about the possibility that Goth!Felicity and Playboy!Oliver might have crossed paths at one point while he was at Harvard and she was at M.I.T.**

_Coffee._

That was the first thought in his mind as he woke up to the early afternoon sunlight glaring through the window. He squinted his eyes against the onslaught, holding his arm in front of his face to ward it off as much as possible. He took stock of his surroundings; he was naked in an unfamiliar bed, and he was all by himself. He sat up and rubbed the sleep out of his eyes. A post-it note fell off his forehead. He blinked a couple of times and picked it up to read the contents.

_My roommate comes back around 1, you should get lost before then. Last night was fun. xo_

He tried to remember who he had hooked up with, but it was lost in a blur of other memories. He remembered going to a party with his frat brothers somewhere off campus, and there was a lot of drinking. And girls. Lots and lots of girls. And he apparently went home with one. The question was, which one?

He rubbed his forehead, trying to massage his hangover away. He was tempted to go back to sleep, but then the thought of coffee from Crema's perked him up and got him moving. He threw off the blanket and turned to the right, placing his feet on the floor. He looked at the clock radio sitting on the night table.

_Shit,_ he thought with only a modicum of alarm. It was almost one o'clock. He got up slowly to look around for his clothes, but then swayed as a bout of nausea threw off his equilibrium. He took deep breaths against the churning in his gut; if there was one thing he hated, it was throwing up. Especially with a hangover, that was the worst. When he tried moving again, his stomach won the battle, and he rushed to the bathroom to expel its contents.

After a few minutes of porcelain praying, he flushed the toilet and stood up to wash his mouth, feeling much better. He turned on the faucet and leaned over the sink, and after a minute he felt like a human being again. He smiled at the Hello Kitty make-up bag sitting on one corner of the sink counter, wondering if it belonged to the girl he hooked up with.

He walked out of the bathroom, and when he saw the door to the room opening, he knew it was too late.

Everything happened at once, but to him, it felt like slow motion. The most beautiful creature he'd ever laid eyes on entered the room. She had jet black hair with a streak of purple on the side. Her perfect pale skin was made more perfect by the dark makeup around her eyes. Her dark red lipstick made her mouth look temptingly kissable. She was wearing a tight tank top that showed off a little belly, and his dick stirred alarmingly.

After that first half-second, her eyes widened with shock and she let out a scream that pierced his brain. He clutched at his head, doubling over as the sound reverberated in his skull.

"Who the hell are you?" she shouted, causing more pain in his head. "And why the hell are you _naked?_"

"Please…" he groaned, "not so loud."

"Never mind," she said, not hearing him. "Don't answer that second one. You must be Alex's latest conquest." She said this in a quieter tone (but still too loud) and with a great deal of disgust.

He glanced up at her, unused to hearing such contempt toward him from a beautiful woman. "Alex?" he repeated. He thought over the women he met at the party, and he couldn't remember an Alex.

She scoffed and shook her head. "I'm not surprised, she doesn't exchange names." Her eyes darted down his body before she looked away sharply. "Please put that thing away. And you're standing in front of my desk. Which is where I need to be."

He was suddenly embarrassed that he was standing in front of this gorgeous woman completely naked, and rushed to find his clothes. As he got dressed, he heard her muttering something about hacking and single rooms.

"You can hack?" he blurted.

She looked over at him, relieved that he was dressed. "Well, I like to call it creative problem solving. Hacking makes it sound dirty."

He grinned. He threw on his playboy charm as he said, "Dirty's not always a bad thing." He was gratified to see a slight blush fill her cheeks.

"Don't you have somewhere to be?" she asked him suspiciously.

He smiled and obnoxiously sat on her bed. She gave him a disgruntled look, but he just smiled at her. "Actually I was hoping to go to Crema Café, care to join me?"

She quirked an eyebrow at him. "Um, that's by Harvard. This is M.I.T."

"Oh!" He blinked, surprised. "Huh." He couldn't remember how he got here, but he was pretty sure he didn't drive. "Well, I guess I'm hoofing it back to Harvard, then. Unless…" He gazed into her eyes soulfully. "You could help a guy out and give me a ride?"

She scoffed at him, unaffected by his charm. "It's not that far. You can walk."

He clutched a fist to his chest. "You wound me!"

"You'll get over it," she retorted, ignoring him in favor of booting up her computer.

He chuckled. "Well, then, can you at least recommend a good coffee shop on the way? I could _really_ use a latte."

She side-eyed him briefly before turning back to her computer. "There's a Starbucks on the corner of Massachusetts and Prospect."

He scoffed. "Boring. Give me another one."

She sighed heavily. "Fine. You should try 1369, it's a couple of blocks from Starbucks."

He edged closer to her, close enough to smell her perfume, which was unexpectedly fruity. "You should join me. Show me what's good there." He added his patented Oliver Queen smile.

She finally turned to look at him and narrowed her eyes. "I have a lot of studying to do. I don't have time for pretty boys."

He grinned widely. "So you _do_ think I'm pretty."

She smiled ever so briefly before turning her mouth down into a scowl. "That's not supposed to be a compliment."

"Ha!" he crowed triumphantly. "I saw that smile. You _like_ me. Don't deny it."

She turned back to her computer with her lips pressed together. "I will admit no such thing."

He stood up and invaded her personal space, leaning over to whisper in her ear. "Come on," he cajoled. "A latte on a Saturday afternoon with me, what do you say?"

She stood up abruptly and he tripped a little backing away. She had a thunderous look on her face, and he suddenly realized this was a woman he couldn't charm easily. She placed her hands against his chest and pushed him toward the door. He sputtered apologies and protests, trying to repair whatever it was that he broke between them. But it did no good.

He was unceremoniously pushed out of her room and the door was about to shut in his face when his hand flew up to stop it. "Wait!" he cried out, pushing his face back into the room. "I never got your name!"

She chewed on her lip thoughtfully. "Felicity. Smoak. Now leave. I really do have work to do."

He smiled dreamily at her. "Nice to meet you Felicity Smoak. Aren't you going to ask for my name?"

She smirked at him. "No. You meet one pretty boy, you've met them all. Now go!"

He took a deep breath and smiled one last time. "I hope I see you around, Felicity."

She shook her head. "Not even if you paid me." With that, she shoved his face and shut the door.

He laughed to himself, staring at the door that separated him from a woman he would likely never forget. And with a unique name like Felicity Smoak, he was sure he would never forget that either.

He turned on his heel and walked away, looking forward to trying out this coffee shop she recommended.


	2. Chapter 2

**A/N: Thank you, all of you, for your overwhelmingly positive feedback on this tiny little story. I think they stayed alive in my head because of your good juju, so really, you gave this to yourselves. XD**

The 1369 Coffee Shop quickly became his new favorite go-to place for his daily latte. He stopped by there most days for his caffeine fix, usually in the early afternoons after he woke up. It was always a quick in-and-out visit, sometimes with a friend, most times not. If he gave thought to Felicity Smoak at all, it was in the back of his mind. He didn't expect to see her there, but there was always a tiny part of him that hoped. He had enough distractions, however, so that the tiniest disappointment in not seeing her quickly fell by the wayside.

It wasn't until about a month later, on his routine caffeine run, that he finally saw her in the coffee shop. A smile spread across his face reflexively, and his heart beat just a little bit faster. She was sitting at a table against the window, her nose buried in a book, and a steaming cup of something in front of her. She looked as gorgeous and alluring as she did the day he met her.

He went to the counter to purchase his latte, and took his drink slowly to her table. He sat gingerly in the seat across from her, careful not to interrupt her, but she didn't look up once. He smiled tenderly, just watching her getting lost in her story. He watched as her eyes darted back and forth across the page, her brows furrowing slightly at some interesting plotline, her lips open and relaxed.

He continued watching her as if he was hypnotized, when she finally lowered her book to reach for her drink and noticed him with a yelp. He jumped a little in his seat at her violent response.

She clapped a hand over her heart, breathing heavily. "You scared the shit out of me!" she exclaimed. "How long have you been sitting there?"

"Only a minute or so," he replied nonchalantly. "You look very nice today."

She rolled her eyes at him. "Still at it, pretty boy?"

He grinned happily. "You remember me!"

She snorted. "Hard to forget you. First time I saw you, you were naked."

He chuckled, and turned on his sly charm. "So you're saying I'm unforgettable?"

She shook her head at him. "You're relentless."

He shrugged. "Some would say persistence is a virtue."

"Mm-hmm," she replied skeptically, raising an eyebrow. "Those same people probably see nothing wrong with stalking, either."

His mouth dropped open. "I'm not stalking you!" he protested adamantly. "I come here all the time."

She raised both eyebrows.

"For the lattes!" he emphasized.

She grabbed her drink and brought it up to her mouth. "Sure," she teased, before taking a sip. "Keep telling yourself that."

He shook his head and laughed. "You think you have some kind of hold over me that I'd stalk you? Please," he added, smirking at her.

"Don't I?" she asked with a coy grin. "Why else would you be sitting here?"

He suppressed a grin and shrugged. "To thank you for introducing me to this little piece of heaven," he replied, waving his arm to gesture at the coffee shop interior.

She smiled into her mug. "It is nice in here."

There was a beat of comfortable silence between them.

"So, can I ask you something?" he ventured cautiously.

She nodded. "Please."

"What's your deal?" At her raised eyebrows, he rushed to clarify. "I mean, why the goth thing? Don't get me wrong, I think it's hot, but people usually have a reason for going that dark. What's yours?"

She narrowed her eyes at him. "Who says I need a reason? Maybe I'm just trying on different styles to see what I like."

He raised a skeptical eyebrow. "Trying to find yourself? Isn't that a little clichéd?"

She shrugged. "What's wrong with clichéd if it's true?"

"See, I don't think that's the whole picture," he remarked, leaning closer.

She leaned in as well, putting her book in her lap and placing her elbows on the table, cradling her mug between her hands. "Well, pretty boy," she challenged, "why do _you_ think I'm doing this 'goth thing'?"

He held his chin in his hand, considering her. "You had overprotective parents who never let you do anything, and you went to M.I.T. because it's far away and you're embracing your rebellious nature in the most extreme way possible to get back at your parents." He finished with a cocky smile, sure he had gotten at least some of those details correct.

She shook her head at him slowly. "The only thing you got right is that this school is far away from home. Everything else is a big negatory."

He snapped his finger. "Damn, I thought I had you pegged."

"Your pegging skills are sorely lacking," she stated dryly.

He chuckled. "I have it on good authority that my 'pegging' skills are far above average."

"Oh yeah?" she teased. "That's what your frat brothers say?" She giggled at her own joke.

His mouth dropped open and he huffed indignantly. "Fine, show me _your_ pegging skills."

"Your kind of pegging skills?" She shook her head with a smile. "No thanks."

He bit his lip, holding back a smile. "The other kind, Elvira."

This time her mouth dropped open. "I'm not even gonna acknowledge that terrible attempt at a joke. Fine, I'll show you my pegging skills." She sat back in her seat, studying him. "Rich kid. Didn't get into Harvard based on merit. Probably an overbearing father who wants you to graduate from an Ivy League for his own reasons, but you're not interested in that."

His face fell, and all the humor of their interaction vanished. He cleared his throat. "Pretty spot on. I'm impressed." He took a sip from his latte and looked out the window.

Her hand fell on his arm, drawing his attention back to her. She had a sincere look of apology on her face. "I'm sorry," she murmured. "I hit a sore spot, didn't I?"

He shrugged it off, pretending her words didn't pierce through the veil. "Nah," he scoffed. "Old news."

"Except it's not," she observed accurately. She rubbed his arm in a manner that was meant to be soothing, but it was only further breaking down his walls and bringing his complicated emotions to the surface. He wanted nothing more than to withdraw his arm and shut down this line of conversation, but he didn't want to lose contact with her hand. He opted to remain still and stoic.

"I'm sorry," she said softly. "You probably don't want to talk about it. You barely know me, and some things are just too raw to talk about." Her voice broke on the last part, making him look up at her curiously.

"You speak from experience?" he asked quietly.

She nodded slowly. "For what it's worth, I think you should do what makes you happy, not your dad. You only get one life, and your dad should stick to running his."

He stared into her eyes, transfixed by the wisdom he saw in them. She was an old soul, and with only a few words, she managed to reach a part of him no one had been able to get to, not since…

"You're pretty wise for such a young kid," he remarked.

She smiled sadly. "I had to grow up pretty fast."

For some reason, that broke his heart. That such a beautiful young creature went through something that forced her to grow up early, that seemed like a crime.

"You're not who you pretend to be," she observed.

The last of his walls fell down with her words, and he felt completely vulnerable with her. It was fitting, in a way. She had seen him physically naked when they met, and now she was seeing him emotionally naked in their second meeting.

"Nobody sees past the pretense," he replied hoarsely.

She squeezed his arm. "You should be with someone who does. You deserve to be seen for who you really are."

He hung onto her words as if they were the very air he breathed. "And who am I?"

She stared into his eyes, looking for his essence. "I don't think you know who you are yet. You're lost. And as long as you keep pretending, you're never gonna find your way home."

He stared intensely at her, suspended in this little moment in time. He heard her words and received them into his heart, letting them plant themselves in his subconscious to bear fruit at another time. "I'm really glad I met you, Felicity," he whispered.

She smiled at him. "I'm glad I got to meet the real you," she replied. "That guy is much more interesting."

He smiled fondly at her.

She leaned back into her chair with a sigh. "Well, I hate to break up this love fest, but I have some coding to do." She picked up her book and mug, draining the rest of her drink. She gave him one last considering look. "Remember what I said. You deserve to be happy, your own way."

He nodded solemnly. He watched her walk away before calling out to her again. "Wait!"

She turned to look at him, nearly at the door.

"You still haven't asked for my name."

She smiled coyly. "I've been calling you Pretty Boy in my head. That's good enough for me." She winked at him and left the café.

He laughed to himself, shaking his head. No, he wouldn't forget her anytime soon.

**A/N: I forsee maybe 2 more chapters. One more of playboy!oliver and goth!felicity, and probably one re-write of episode 1x03. **


	3. Chapter 3

**A/N: Huge thanks to justanother90sbaby on Tumblr for being my beta for this chapter! I was totally overthinking some things and she brought in some much needed perspective. Hope you like it. (I may have stayed up all night writing this hehe)**

After Oliver's last conversation with Felicity, he spent an entire week tossing and turning at night. Her words kept haunting him, and he knew he had a decision to make. He was at a crossroads in his life, but he didn't like any of the options before him.

He called in emergency help, urging his best friend to hop on a jet to meet him in Cambridge. They met at Oliver's favorite table in his go-to coffee shop, both sipping on his beverage of choice.

Tommy nodded his head in appreciation. "You're right, this _is_ good."

Oliver smiled. "Told you, man. Best latte in town."

"How'd you find this place?"

"A friend," he replied, smiling enigmatically.

"Uh huh." Tommy raised an eyebrow, giving him a knowing smirk. "A lady friend, perhaps?"

Oliver shrugged. "Maybe."

"Let me guess," he said, throwing up his hands. "She brought you here the morning after."

Oliver shook his head with a smile. "No, actually. We've never hooked up."

"What?" The omission earned an indignant cry from Tommy, "You losing your touch, man?"

He shook his head again. "It's not like that, not with her."

"Woah," Tommy replied, taken aback. "Who are you, and what have you done with Ollie?"

Oliver shrugged. "She's just different."

Tommy threw up a hand again. "Dude. You are not allowed to fall in love or become some whipped, lover boy. We're still young! We're in our prime! I need my wing man!"

"It's not like that either," he reassured. "Jesus, calm down."

Tommy pulled up his sleeves and leaned forward. "Okay, good. Now, is this girl the reason you asked me to fly three thousand miles to see you?"

"No," Oliver replied, before correcting himself. "Well, not exactly."

Tommy raised his eyebrows. "Explain."

Oliver leaned back in his chair and sighed. "I'm thinking about dropping out." He looked at Tommy, waiting for his reaction.

He didn't say anything, waiting for him to continue. "Is that it? Or is there more?"

He rubbed his forehead, the arguments in his mind circling around and around again. He decided to let it all out, figuring Tommy could help him process his thoughts.

"It came up in conversation that I'm not thrilled being at Harvard, and she suggested that I should try and find happiness my own way. So I'm thinking of dropping out. But if I do that, my dad will be pissed, and I'm worried that he'll cut me off. Which he all but threatened to do.

"But I hate being here—with one exception. This girl I met. She's the only reason I would stay, but I know that's not a good enough reason. Besides, she's crazy smart, and I feel like I wouldn't have much to offer her if I dropped out. And if I did drop out, and my dad did cut me off, I'd basically be a homeless nothing, and then I wouldn't feel right pursuing a girl like Felicity. But the thought of staying in school just kills me inside, and I really, _really,_ don't want to work for my dad, but the thought of dropping out and moving back home, so far away from Felicity makes me just as sad, and fuck..." He dropped his head in his hands. "I don't know what to do."

The silence between them stretched out, far longer than Oliver was comfortable with. He lifted his head to look at his best friend, finding a contemplative look on his face.

"Well?" Oliver prompted.

Tommy took a deep breath and sighed, folding his hands in front of him. "Ollie. You know I love you, right?"

He nodded.

"And, nobody knows you like I do, would you agree?"

He nodded again.

"Dude. This is not the first time you've had this crisis. You remember Rebecca at Brown?"

Oliver sank in his seat. He nodded again, sulking a little this time.

"Or Jenny at UCLA? Laurel after graduation?"

His head returned to his hands. "Okay, okay, what's your point?"

"My point, Ollie, is that you fall in love really easily. I mean, I get it. Your parents didn't pay enough attention to you, so when a beautiful woman gives you that kind of attention, you soak it up like a sponge, and you think you're in love, but buddy…" He slapped him on the shoulder. "You're just infatuated."

A part of Oliver wailed against his friend's logic, not ready to let go of the idea of Felicity Smoak. "But what if this one's different?"

Tommy pinched the bridge of his nose. "So what if she is? Are you anywhere near ready for her?"

Oliver didn't have anything to say to that.

"Look," Tommy said, softening his voice. He leaned closer to Oliver, looking directly into his eyes. "You need to figure out what you want for yourself before you go looking for love, because let me tell you, man…a woman is not going to fix everything."

He looked at Tommy skeptically. "Where the hell do you come up with this stuff?"

His friend threw up his hands indignantly. "What? I watch Dr. Phil!"

Oliver laughed. "Jesus, Tommy, you cannot be spouting Dr. Phil at me right now."

"Say whatever you want, that guy knows a thing or two. Besides, I know what I want. I want to have a good time while I'm young, and when I meet the _right_ girl, that's when I'll settle down. Until I meet her, I have no interest in doing shit."

Oliver shook his head. "The wise words of Tommy Merlyn, everyone."

"Fuck you, man. You know I'm right."

Oliver rubbed his head. "And what about my dad, and school?"

"Fuck, I don't know. Maybe you should talk to your mom first, play on her emotions. Get _her_ to talk to your dad."

Oliver chuckled. "Jesus," he muttered. "You're a manipulative son of a bitch."

"Hey," he defended, "I'm my dad's son. I can't help it."

Oliver's fingers continued to worry the skin over his eyebrow. "So I should just walk away from this girl?"

Tommy sighed again. "What the hell would you do if you stayed? Who says she's even looking for a relationship? Or that she's interested in you that way?"

"I think she's interested."

"Ollie, you're not listening to me. You're still hanging on to your infatuation. You're like a kid with a fixation, and you want to have it now. I get that, too, because we're both spoiled rich kids used to getting our way, but women are not things. I know it's hard for you to realize this, but she's not your one and only."

A part of Oliver couldn't accept that. "But what if she is?"

Tommy rubbed his face with his hands. "If you were meant to be with her, if she really was your one and only, then fate will find a way to bring you two together, when you're both ready. But you. Are. Not. Ready." He punctuated each word with a finger to Oliver's shoulder.

Oliver thought for a moment, shaking his head in wonder. "How is it that you're the wiser one of us?"

"I'm not wiser, Ollie," Tommy smirked. "I'm just more practical. You're the romantic."

Oliver huffed a laugh. "Oh yeah. That's why we work so well together."

"Exactly," his friend agreed emphatically. "We're two sides of the same coin. Frick and Frack. Mike and Ike."

Oliver sighed. He knew what his decision was. He could always trust Tommy to lay it out in black and white for him. "Wanna come help me pack?"

Tommy looked up from his latte in surprise. "Really? Just like that?"

Oliver shrugged. "I'll just hitch a ride with you. No sense postponing the inevitable."

A slow smile crept over Tommy's face. "All right! Starling's most eligible bachelors are back in business!" They slapped their hands together and then pulled them apart. "You have so much catching up to do!"

Three hours later, Oliver was done packing. As his possessions were taken out to the limo, he shared a few final shots with his frat brothers. He had announced cavalierly that he didn't feel like being in school anymore and was going to spend some time living free of responsibility, to which they all toasted to him boisterously. He was going to leave his mark at Harvard like he had left his mark on the other universities; the legendary Oliver Queen, playboy billionaire.

It was all a mask, and a familiar one at that.

He only had one more stop before leaving Cambridge forever. To see someone who saw behind the mask.

The limo stopped in front of her dorm. The door was opened for him, and he looked at Tommy. "Do you want to meet her?" he asked tentatively.

"Do you want me to?"

He thought about it for a second, and then nodded his head. "Maybe you'll see things differently and tell me I'm crazy."

Tommy shrugged. "All right."

Butterflies attacked his stomach the entire way up to her room. He took deep breaths, trying to control his anxiety. He knew this was the right thing to do, but he couldn't help feeling a bit panicked at the thought of letting her go.

"Jesus, look at you," Tommy remarked, smirking at him. "You really do like her, don't you?"

He ignored him completely, keeping his mind on the words he was practicing in his head. They reached her door, and he hesitated a couple of times before knocking. With a final deep breath, he rapped on the door.

A busty blonde opened the door, one that he recognized. She looked Oliver over with a smile. "Hey," she said, leaning against the doorway. "Come back for seconds?"

Out of the corner of his eye, he could see Tommy checking her out approvingly. "Uh, no," he replied quickly. "Actually, I'm here to see Felicity."

She scoffed at him. "Why?"

Oliver clenched his jaw. "Is she here?"

She rolled her eyes at him and turned away. She spoke to someone inside. "You have a visitor."

Tommy slapped Oliver's arm, staring at him. "You hit that?" he mouthed.

"Shut up," he whispered through clenched teeth.

Felicity showed up at the door and looked at both of them in surprise. "Oh, hi." She looked at Tommy, and then back at Oliver. "A friend of yours?"

Oliver smiled. "Yeah. This is—"

"Ah!" she interrupted. "Why mess with a good thing?" She looked at Tommy again. "I'll just call you…the cute one."

Tommy grinned at her and laughed. "What?"

"Oh, he didn't tell you?" She tilted her head at Oliver. "I call him Pretty Boy."

Tommy looked at Oliver with a wide grin. He looked back at Felicity. "So, he's pretty and I'm cute?"

She shrugged. "Sure, why not."

Tommy extended his hand. "Well, it's very nice to meet you. May I call you gorgeous?"

She shook his hand and rolled her eyes. "Oh my god, did you both go to the same lame charm school?"

Tommy raised his eyebrows in surprise. "Is this how you talk to all the guys?"

"Aw, worried that you're off your game?" she teased. "Here's a tip. Lines don't work. Not on real women."

He laughed out loud. "Wow. You're incredible."

She shook her head. "See, this is why I weep for future generations. I insult you and you're impressed? Somewhere in your past, somebody crossed the wires."

He stared at her, and then looked at Oliver. He shook his head, reeling from the conversation. "I'm gonna wait in the limo." He turned back to Felicity. "It was a pleasure meeting you, Felicity. And I can promise you, that isn't a line." He winked at her, patted Oliver on the shoulder, and walked away.

She looked at Oliver, impressed. "A limo, huh? So I was right about the rich kid thing."

Suddenly being alone with her brought back all the butterflies. "Yeah," Oliver said breathlessly. "Can I talk to you? Privately?"

"Uh, okay," she said tentatively. She stepped out of the room and closed the door behind her. "There's a common room at the end of the hall, it might be empty."

He just nodded and followed her lead.

The room was indeed empty, and they sat on a couch in the far corner. He rubbed his hands on his trousers, taking a deep breath. "So," he began, "I thought a lot about what you said, and I decided that I'm dropping out."

"Oh!" she replied, wide eyed with surprise. Did he detect a hint of disappointment? "That's…that's good, right?"

He took another deep breath. "We'll see. I still have to face my parents. There's no telling how that's going to go."

"Still," she encouraged, "it's a big step. You're taking charge of your own life."

He looked down at his hands. "Yeah," he replied softly.

"Hey." She placed her hand under his chin and lifted his head. "Why the sad face?"

He shrugged. "I'm just glad I met you, and I'm sad that I have to leave."

She smiled at him. "Well, that's the way these things happen sometimes. People come and go in our lives. Some stay for a while, others pass through in an instant. We can't hold onto the ones that pass through, because they're meant to be ephemeral."

"How can you tell the difference?"

She shrugged. "Time, I guess? I don't know. I don't have the answer for everything," she added with a giggle.

He laughed. "Could have fooled me." He looked down at his hands. Something Tommy said just occurred to him. He looked back up at her. "Do you believe in fate?"

She looked distantly at a point past his shoulder, thinking about his question. "I think that there are some things that can't be explained as a coincidence, but at the same time I believe we choose our own fate. So, yes and no?"

He smiled. "I guess what I mean is, if two people were meant for each other, do you think fate would bring them together when they're ready?"

She shrugged. "Who knows? I don't know. Maybe? Sounds like a romantic idea."

"That's what my friend calls me—the romantic."

"Does he, now?" she teased.

Oliver shrugged. "I don't know. The thought comforts me a little." He looked at her meaningfully.

She smiled warmly at him. "Well, like I said. Who knows?"

He nodded, and stood up reluctantly. She stood up with him. "I should get going," he said.

"Okay," she replied. She stepped forward and wrapped her arms around him, surprising him with her affection. He swallowed the lump that formed in his throat and wrapped his arms around her. _Please let me see her again,_ he prayed helplessly to whatever deity would listen.

"Take care of yourself, Pretty Boy," she murmured.

He laughed. "Are you still not going to ask for my name?"

She released him from the hug and looked up at him with laughter in her eyes. "Tell you what. Next time you see me, you can tell me your name."

He laughed again and nodded. "It's a deal."

Before he could talk himself out of it, he swiftly bent down and kissed her on the lips. He pulled away just as quickly, and saw her blushing slightly and biting both lips. He gave her a cheeky wink before turning around and walking to the door. He stopped one more time and looked back at her.

"See you around, Felicity Smoak." And with that, he left the room with hope in his heart.

**A/N: I may have lied about how many chapters are left. Well, maybe not. But I think there will be a short interlude before the 1x03 rewrite, because Tommy and Oliver are still talking to each other in my head, and they won't shut up until I write it down. (Plus I miss Tommy and he's so much fun to write.)**


	4. An Interlude

**A/N: Damn. I made myself cry with this one.**

Tommy's first words when he re-entered the limo were, "Dude, she is a force of freakin' nature!"

Oliver chuckled. "She packs a punch, that's for sure."

"How exactly did you meet her? And when did you bang her roommate? And where does that fit into all this?"

Oliver put up his hand to slow him down. "It's not really a long story. I slept with the blonde chick and I was still in their room when I met Felicity."

"And how did that turn into you being jello with her?"

"Jello," he repeated under his breath, shaking his head. "Whatever, I thought she was hot, and I tried to ask her out, and she said no."

"What, and you thought that was a challenge or something?"

"No!" He shook his head, trying to find the words to explain. "I don't know, it happened kind of fast. She just got into my head."

"Nope," Tommy objected. "You're definitely leaving out some details. You're not telling me the whole story. I demand that you spill."

Oliver sighed. "I…might have…been naked when we met."

Tommy's jaw dropped and his eyes widened. "Get the fuck outta here. She saw all of that," he remarked, gesturing to his groin, "and still said no?"

The corner of Oliver's lips ticked upward. "She said, and I quote, 'Put that thing away.'"

Tommy doubled over, laughing hysterically. He swiped at his eyes. "Holy shit! What did you do, strut your stuff?"

"No!" His face reddened at the memory. "I got dressed. It was pretty embarrassing." His eyes went distant as he recalled that day. "And then I tried asking her out. And she shut me down. Several times. I even did the thing where I whispered in her ear, and I think I fucked up because then she was pushing me out of her room, and she shoved my face." He chuckled.

"Holy shit," Tommy repeated, still shaking with laughter. "I like her, Ollie. I might have been wrong about her."

Oliver turned an angry gaze on his friend. "The fuck?"

Tommy threw his hands up in defense. "Woah! This changes nothing, man. My words of wisdom still stand. I'm just saying, I totally get why you're crushing on her. That's all."

Oliver was mollified for now.

"That doesn't explain why you're jello, though. Something changed."

Oliver smiled. "The second time I saw her was in that coffee shop. It started about the same, me trying to charm her, her shutting me down…but then…"

"School, and, I'm guessing, dad?" Tommy guessed correctly.

Oliver nodded solemnly.

"Aw," Tommy sympathized sarcastically. "She saw your mushy insides."

He punched his friend's shoulder, hard. "Fuck you, man."

"Ow, Jesus!" Tommy rubbed his shoulder. "Okay, I see it now. She saw your mushy insides and you melted like a snowman in July, ergo, she got under your skin."

Oliver closed his eyes, grieving a little for the possibilities he left behind.

"Hey," Tommy blurted, shoving his shoulder. "Don't go there, man. You have a lot to look forward to. Focus on you, not her. Focus on what you're gonna say to your mom, because we both know you'll talk to her first, and then think about what you want to do with your life. That's what you need to think about. Leave Felicity at M.I.T. I have a feeling she can take care of herself."

He wallowed in his grief, in rebellion to Tommy's words. "I can't just have a moment? One little moment to mourn what could have been?"

Tommy sighed, relenting. "Okay, you big marshmallow. Come here." He opened his arms, beckoning him over.

Oliver resisted at first, trying to hold onto his pride, but Tommy would have none of it.

"Come on, you big wuss! We've seen each other naked, and it's not our first cuddle. Get over here."

Oliver let down his walls and cuddled into Tommy's embrace, and let himself cry for what could have been.

Tommy shushed him and stroked his head. "It's gonna be okay, Ollie. You'll be able to move on, you always have. It's okay." He continued shushing and stroking his head, protecting his brother in his moment of vulnerability.

**A/N: I thought briefly of spacing this out because I _just_ posted Chapter 3, but these guys talked so fast that this came a little too easily, and really, who couldn't use some Tommy x Oliver brotp in their lives?**


	5. Chapter 4

_Felicity Smoak._

Oliver stared numbly at the name that immediately caught his attention like a fish on a hook. He blinked a few times, trying to clear his vision, convinced that his eyes were playing tricks on him. It wasn't possible that she was working at his family's company, was it? He pulled up her file, searching for a picture. The face that came back was vaguely familiar, but he wasn't sure. For one thing, this woman was blonde. And she wore glasses. It didn't match how he remembered her. Maybe she had a twin? Maybe she had given him a false name; after all, she never asked for his.

He went online to search for her, to find any other pictures or websites with information, but he didn't find anything. She certainly didn't leave much of a digital footprint. He pulled up her personnel file again, and that's where he found it.

M.I.T., class of '09. Masters in Cyber Security and Computer Sciences. It was her.

His heart beat faster in his chest. He shook his head, still unable to accept this twist of fate. It was too much information to process, and he couldn't get a handle on his thoughts or emotions. He felt paralyzed, staring at the computer screen, unable to decide on his next move. If only Floyd Lawton hadn't completely obliterated the laptop with bullets…

The mission. That was what he needed to focus on. He needed to take down Floyd Lawton. He needed access to whatever was on that laptop. But he needed someone's help. The strategist inside him knew that going to the best and brightest in QC's IT department was the right option. But the man inside him…

He was paralyzed in his thoughts again. Everything stopped when he thought of her. He couldn't move forward with his mission until he figured out how to move past the wall in his mind, blocking him from processing his…feelings, or whatever.

He backed away from the desk roughly. He got up and took off his shirt. He needed to work out and clear his mind.

He was two sets into his salmon ladder rotation when his mind wandered to that fateful day that he met Felicity Smoak. He knew that as long as he lived, he would never forget the moment he laid his eyes on her. It was like seeing a beautiful, dark angel, a creature that was more than human. He remembered with amusement how she had shut down all his advances, even as he sensed that his advances were not unwelcome. He remembered with a laugh how she had physically thrown him out of her room, and the way it felt to have her delicate hand on his face as she shoved it.

He jumped off the salmon ladder with a grunt, shaking his head from his thoughts. This wasn't working. He decided to spend some time sparring against the steel beams with his blades. He hoped the noise would be enough to drown out his thoughts so he could find his center.

He focused on the rhythmic clanging of steel and the vibrations in his hands as he moved through the most complicated kata that he knew. He paid attention to his breathing and his footwork, and little by little, he felt the cold cloak of clarity descend on his consciousness, clearing away any confusion. The mission had to come first. Any discomfort he experienced as a result of who he asked for help was irrelevant. Floyd Lawton needed to be stopped. As long as he kept that in the front of his mind, everything else wouldn't matter.

He consciously brushed aside any thoughts that argued otherwise.

* * *

><p><em>He was lost in a maze of steel beams, chasing after an elusive figure. Voices floated through the air, snippets of conversations from long ago.<em>

_"Do you believe in fate?"_

_"She's not your one and only!"_

_He caught a glimpse of raven hair and a lithe figure before losing her again._

_"We can't hold on to the ones that pass through."_

_"I can't just have a moment?"_

_A feminine giggle echoed in the maze, and he redoubled his efforts to find her._

_"As long as you keep pretending, you're never gonna find your way home."_

_"I'm sad that I have to leave."_

_Movement on his right drew his attention, and he caught a flash of blonde._

_"Please let me see her again."_

_"Fate will find a way."_

_"Oliver?"_

_He was standing in the foyer of his house. His mother walked toward him with a look of surprise. Her hair was longer, the way it had been before the island._

_"What are you doing home so early?"_

_"Mom, I can't keep pretending. I don't want to work for the company."_

_She looked at him, disappointed but unsurprised. "I'll talk to your father."_

_He hated that look. He saw it far too often._

_It was no longer his mother that stood before him. It was Laurel instead._

_"What do you mean you don't want to live with me?"_

_"I'm sorry, Laurel, I don't want to pretend anymore."_

_Hurt and anger filled her expression. "Screw you, Ollie."_

_A flash of lightning brightened the room for a moment. He turned and saw his father. They were on the yacht. His father put his arm around him and patted his chest. "You're lost, son."_

_"I know, a good friend once told me that."_

_Another flash of lightning. They were on the raft._

_"I didn't save the city! I failed it!"_

_His father raised a gun to his own head._

_"Dad! NO!"_

* * *

><p>He shot up in bed, gasping for breath, the sound of the gunshot still echoing in his ears. He was shaking from the images that still haunted him. He jumped out of bed and stalked into the en suite to splash cold water on his face. For a micro-second, he saw his father, dead and bloated, when he looked in the mirror. He shut his eyes immediately, trying to think good thoughts, to replace that image with better ones. Tommy's happy and slightly manic face came to mind, and he was able to take a deep breath. He looked reluctantly at the mirror again, and was relieved to see himself, still pale from his nightmare. Well, not quite a nightmare. More like memories coming to the surface.<p>

The sun was just starting to peek over the horizon, so he decided to get started on his morning. As he went through his routine, he thought about the memories his mind stirred up, particularly the ones about Felicity Smoak. He thought about the day he left Cambridge, about the conversations he had with Tommy, and then Felicity. He might have believed in fate back then, but the last five years burned away any romanticism in him. Now, he wasn't sure.

He remembered her words about the topic, that some things couldn't be explained as coincidence. Was the fact that she was an employee of QC a coincidence? Or fate?

He thought about Tommy's words to him in the coffee shop. That if she really was his one and only, fate would find a way to bring them together when they were ready. That was the punch line, wasn't it? He wasn't ready for her then, but he was even less ready for her now. There was not the slightest chance in hell he could deal with a relationship, not now. Maybe not for a very long time. Was fate cruel, then? To bring her back into his life at a time when she should stay as far away from him as possible?

He shook off his thoughts and walked into his closet to get dressed. He couldn't think about this right now. He had a job to do, and he needed to pull himself together. He did his best to empty his mind and recapture the cold logic from last night, but he knew he was deluding himself if he thought he could remain stoic about this meeting.

* * *

><p>He stepped off the elevator at Queen Consolidated with his heart in his throat. He walked slowly toward the IT department, the bullet-ridden laptop tucked against his side and the fingers of his other hand rubbing together compulsively. He asked the first person he saw for directions to her office, and with every step his heart beat harder and faster in his chest. He took deep breaths to maintain his composure. He just had to remember the words he practiced on the way over, and everything would be okay.<p>

He finally stepped through the doorway to her office, and the first thing he noticed was her perfume. It was fruity and floral, not the exact fragrance he remembered her in, but in the same family. He was transported briefly to the moment he sat in her room, watching her profile as she did the same thing she was doing now, concentrating on a computer monitor.

Her blonde hair was pulled back in a ponytail, and she was wearing glasses. There was a red pen in between her brightly painted lips. She had on a very professional looking pink button down shirt with her QC badge hanging around her neck. He had a hard time reconciling this Felicity with the one who stayed in his thoughts the last seven years.

He cleared his throat to get her attention. "Felicity Smoak?" he asked tentatively.

She turned to face him, and the expression on her face as she pulled the pen out of her mouth did it for him. He finally recognized her. He recognized the bright blue of her eyes as she looked at him with shock, the shape of her lips as her mouth dropped open. It was the same exact expression he saw for a fraction of a second the first time they met, and again when he surprised her at the coffee shop.

"Hi," he said in a breathy gust. He grinned widely, and just like that, he felt a little bit like his old self. Before the shipwreck, before the island, when his biggest problem was deciding what he wanted to be when he grew up.

He saw that she recognized him, and he laughed a little when she mouthed 'Pretty Boy' with an incredulous expression. He remembered his promise to her the last time he saw her, and he decided to fulfill that promise.

"I'm Oliver Queen."

* * *

><p><strong>AN: Thank you all for your patience in waiting for this chapter! This ends this portion of the story; I thought it was nicely symmetrical with the endings of the other chapters. I will most likely continue this, but it's going to have to wait a bit, because poor Oliver in Second Date is gonna burst if I don't take care of him soon. (Plus I'm super anxious to get them to their third date.)**

**Just a quick thanks to justanother90sbaby for lending her eye on this chapter, and mabscifiromantic for the lovely comment!fic on AO3 that I referred to a couple of times for inspiration.**

**Also, for those of you who don't already know, I started a forum to serve as a message blast to all of you regarding my fics. So many of you sent me love for this story and asked for this update, and I wanted to so badly to talk to you about it, but the messaging system here is underwhelming. It's in the Arrow forums, called Skimmy77's Forum. I'm test driving it, so let me know if it works for you.**

**EDIT: To the guest who asked if I'm ever going to update, I've left a response in my forums under the thread "Addressing Comments to First Impressions." Short answer, yes. Eventually.**


End file.
